Diastereo- and Enantioselective Synthesis of β-Aminoboronate Esters by Copper(I)-Catalyzed 1,2-Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines

作者: Jeongho Kim , Kwangwook Ko , Seung Hwan Cho

DOI: 10.1002/ANIE.201705829

关键词:

摘要: Reported herein is an efficient copper(I)-catalytic system for the diastereo- and enantioselective 1,2-addition of 1,1-bis[(pinacolato)boryl]alkanes to protected imines afford synthetically valuable enantioenriched β-aminoboron compounds bearing contiguous stereogenic centers. The reaction exhibits a broad scope with respect 1,1-bis[(pinacolato)boryl]alkanes, thus providing β-aminoboronate esters excellent enantioselectivity. synthetic utility obtained ester was also demonstrated.

参考文章(52)
Jack Chang Hung Lee, Ho-Yan Sun, Dennis G. Hall, Optimization of Reaction and Substrate Activation in the Stereoselective Cross-Coupling of Chiral 3,3-Diboronyl Amides. Journal of Organic Chemistry. ,vol. 80, pp. 7134- 7143 ,(2015) , 10.1021/ACS.JOC.5B00991
Alexey S. Gorovoy, Olga V. Gozhina, John S. Svendsen, Anna A. Domorad, George V. Tetz, Victor V. Tetz, Tore Lejon, Boron-containing peptidomimetics--a novel class of selective anti-tubercular drugs. Chemical Biology & Drug Design. ,vol. 81, pp. 408- 413 ,(2013) , 10.1111/CBDD.12091
Alexey S Gorovoy, Olga Gozhina, John‐Sigurd Svendsen, George V Tetz, Anna Domorad, Victor V Tetz, Tore Lejon, None, Syntheses and anti-tubercular activity of β-substituted and α,β-disubstituted peptidyl β-aminoboronates and boronic acids. Journal of Peptide Science. ,vol. 19, pp. 613- 618 ,(2013) , 10.1002/PSC.2537
Ranjan Jana, Tejas P. Pathak, Matthew S. Sigman, Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chemical Reviews. ,vol. 111, pp. 1417- 1492 ,(2011) , 10.1021/CR100327P
Daniele Leonori, Varinder K. Aggarwal, Lithiation-borylation methodology and its application in synthesis Accounts of Chemical Research. ,vol. 47, pp. 3174- 3183 ,(2014) , 10.1021/AR5002473
Ferruccio Bertolini, Paolo Crotti, Valeria Di Bussolo, Franco Macchia, Mauro Pineschi, Synthesis and cyclodehydration of hydroxyphenols: a new stereoselective approach to 3-aryl-2,3-dihydrobenzofurans. Journal of Organic Chemistry. ,vol. 72, pp. 7761- 7764 ,(2007) , 10.1021/JO070316Q
Kohei Endo, Takahiro Ohkubo, Munenao Hirokami, Takanori Shibata, Chemoselective and regiospecific suzuki coupling on a multisubstituted sp3-Carbon in 1,1-diborylalkanes at room temperature Journal of the American Chemical Society. ,vol. 132, pp. 11033- 11035 ,(2010) , 10.1021/JA105176V
Bowman Potter, Adam A. Szymaniak, Emma K. Edelstein, James P. Morken, Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides. Journal of the American Chemical Society. ,vol. 136, pp. 17918- 17921 ,(2014) , 10.1021/JA510266X
Jack Chang Hung Lee, Robert McDonald, Dennis G Hall, None, Enantioselective preparation and chemoselective cross-coupling of 1,1-diboron compounds Nature Chemistry. ,vol. 3, pp. 894- 899 ,(2011) , 10.1038/NCHEM.1150